You Better Tell Me
by Latishiante1001
Summary: You have been hunting with the Winchesters for a few years now and have had a crush on Dean for 3 of them. Once you flirt with a cute waiter, something you never thought would occur, happens.


"My name's Jason and I will be your waiter today. Have you figured out what you wanted yet?" Your waiter, Jason, said while eyeing you.

You'd have to admit that he's kinda cute. He was tall, thin but kind of muscular. He had a nice smile and glasses. He looked like a cute nerd. You were a sucker for cute guys with glasses.

"Uh, I'll have the special with a side of bacon and coffee, please." Dean says, not looking at the waiter.

Jason jots that down in his notepad before looking at you, "And you miss?"

"Oh, um. I will have the grand slam with a side of bacon and coffee." You tell him and he jots it down in his notepad.

"Alrighty, comin' right up." Jason says before starting to walk away.

"Thanks Jason." You say, turning towards him and giving him a wink. He smiles and winks back.

You turn towards Dean again and he's looking at you with an unreadable face.

"What?" You ask.

"Are you really flirting with the waiter?" Dean asks you, his surprise slowly turning into anger.

"Yeah, he's cute." You say and Dean scoffs. "What do you care? You can't judge me when you hit on everything that moves."

"I'm not judging! You've just never done that before." Dean defends, looking down, trying not to get mad.

"Yeah, and? Maybe I wanna have a little fun, too."

You look away and cross your arms over your chest.

 _I wonder what's with him? Being in my business. Maybe he- no! I will not think that and get my hopes up._ You sigh quietly and look at Dean, wishing that he might be jealous and like you back. _He's just protective. He doesn't want you to get hurt._

"Here's your coffee. It's a bit hot so be careful. Your food will be out in a bit." Jason says, looking at you for a minute before putting your guys' coffee down.

"Thanks Jason." You say again, testing Dean. Dean looks up sharply when he hears you and then looks at you. When you turn back around, Dean looks at his coffee.

~~~~ 15 (agonizingly quiet) minutes later ~~~~

"Okay, here we go. We got the special here for you. And the grand slam for the pretty lady here. And here is your guys' bacon. Do you need any extra butter or anything?" Jason says as he puts your food down.

"I'm good." Dean responds.

"I'm fine. Thank you." You say, picking up your knife and fork.

When Jason walks away, you watch him go before looking at your food. Dean looks at you for a minute before starting to eat his food. You join him and for the rest of the meal it is silent.

~~~~

You heave a sigh as you collapse onto the bed in the motel room you and Dean are sharing. Dean walks in and takes his jacket off and collapses on the other bed.

You are close to falling asleep when Dean speaks up.

"Y/N, did you really like that waiter?"

You turn to your side and look at him.

"What?"

"Did you like that waiter?" Dean repeats, turning to his side to look at you.

"No. I mean, yeah, he was cute but I never _liked_ him. Why?"

"Just asking." Dean says before laying on his stomach.

"Dean. You've never 'just asked' something like that before. What is it?" You ask, sitting up.

"It's nothing." Dean murmurs into the mattress.

You sigh and sit next to him on his bed. "Dean, just say it."

"No. I told you it's nothing."

"Then why are you laying on your stomach and pouting."

"I'm not pouting."

"That sentence had 'pout' written all over it."

"No, it didn't."

"Alright, then tell me what's on your mind." Dean moves his head back and forth. "You better tell me."

"Why?"

"Oh, I don't know. Maybe because of this!" You say before starting to tickle Dean. Dean starts to laugh and writhe on the bed.

"Haha! Stop! Please! Stop!" Dean protests while laughing. You keep tickling him, laughing yourself.

You keep this up for a few more minutes before stopping as Dean starts to cry from laughter. Dean rolls away from you after you stop. Dean is holding his midsection while he laughs it off.

"Oh my god. My stomach hurts so bad. Why would you do that to me?! That was evil." Dean chuckles.

"So that you would stop pouting and tell me why you asked if I really liked that waiter." You respond, bringing the topic back up.

Dean sobers up as you speak and sits up to look you in the eye.

"You wanna know why I asked if you liked that waiter?"

"Yes, please."

"Because I've been in love with you since I met you." Dean answers seriously.

You were sure that your eyes were bulging out of your skull. You couldn't have heard him right. Did Dean just say that he's in love with you? There's no way.

"D-Did you just say that you're in love with me?" You ask softly.

"Yeah. Yeah I did." Dean replies just as soft. "Is that okay?"

You grin, "Yeah. Yeah it is. You wanna know why?"

"Why?" Dean asks starting to smile.

"Because I've been in love with you too." You admit.

Dean gives an exhale and falls back onto the bed, "Oh, thank god. I thought I was going to have to jump out of the window."

You chuckle and lean over him, "You and me both, Dean. You and me both."

You bend down and brush your lips against his. You are about to pull back but Dean places his hand on your neck to bring your lips to his and kiss you properly. You move to straddle him and kiss him deeper.

The night ensues into some of the best sex you have ever had with the friend you now know as, the love of your love.


End file.
